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53 Flag Hill Road

Colebrook, Connecticut 06021

ACTIVE - NEW$269,900
Beds
0
Baths
0
SqFt
Acres
27.21
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Discover an exceptional opportunity to create your own private country estate on 27 beautiful acres in the charming Litchfield Hills. Bordering protected Land Trust property an backed by a wildlife preserve, this remarkable parcel offers an extraordinary sense of seclusion, privacy, and connection to nature-yet provides the flexibility to bring your vision to life. Located at the end of a cul-de-sac, the property features a natural, regular configuration with a picturesque stream meandering east to west through the center of the land. Approximately two acres of cleared, buildable area provide an ideal setting for your dream home, while an existing 350 feet of finished driveway leads toward the homesite, with an additional 350 feet of roughed-in driveway already in place. With its open land, wooded acreage, natural water feature, and exceptional privacy, the property is ideally suited for a private estate or horse farm. There is also potential for subdivision and development, offering an attractive opportunity for those seeking both long-term flexibility and investment potential. The property is designated **PA 490 Forest Land**, providing a valuable property-tax reduction. A septic and soil test, property survey, and wetlands survey covering the first third of the property are on file. This extraordinary 27-acre parcel offers the rare combination of privacy, natural beauty, infrastructure, and potential that is increasingly difficult to find in the Litchfield Hills.

Key Facts

City/Town
Colebrook
Neighborhood
N/A
Property Type
Land
Days on Market
0 days
Beds
0
Baths
0 baths
Lot Size
27.21 acres
Property Taxes
$921 / Annually

Market Snapshot

The Colebrook Market

Land · trailing 12 months

Median Days on Market

212

6 active listings

Median $ / Sq Ft

--

6 active listings

Sale-to-List Ratio

80.2%

3 sales

How this home compares

List Price

$269,900

vs $522,500 median

48.3% below median

Price / Sq Ft

--

Median unavailable

Limited comparable data

Days on Market

0 days

vs 212 days median

212 days fresher than median

Based on 6 active and 3 closed sales (trailing 12 mo) of land in Colebrook. Source: SmartMLS · As of August 29, 2026.

Location

53 Flag Hill Road, Colebrook, Connecticut

Property + 3 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,555

per month

  • Principal & Interest$1,388
  • Property Taxes$77
  • Insurance$90
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Colebrook
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Land
Subtype
SingleFamilyResidence

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Exterior & Lot

Lot Size
27.21 acres
Zoning
R2
Waterfront Details
Not Applicable
Water Source
Well Required
Sewer
Septic Required
Flood Zone
No
Lot Description
SecludedAdditional Land Avail.On Cul-De-SacRolling

Listing & Financials

Property Taxes
$921 / Annually
Days on Market
0
MLS #
24202868
MLS Status
Active

Similar Properties

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Listed By

Candice Slatt

(203) 340-1132

Century 21 Scala Group

(203) 374-9451

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 8/29/2026 at 11:31 PM UTC.